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Cheap flights from Chicago Midway Airport to San José from $90

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to San José departing on 4/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago Midway Airport to San José

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
2:56 pm - 12:12 pm
MDW
-
SJO
22h 16m
1 stop
Frontier Logo
9:35 am - 10:02 pm
SJO
-
MDW
35h 27m
2 stops
$395Frontier
Wed, Apr 8 - Fri, May 29
Frontier Logo
2:56 pm - 12:12 pm
MDW
-
SJO
22h 16m
1 stop
Frontier Logo
10:06 am - 11:05 pm
SJO
-
MDW
11h 59m
1 stop
$426Frontier
Sat, Apr 4 - Sat, Apr 11
Frontier Logo
2:56 pm - 12:12 pm
MDW
-
SJO
22h 16m
1 stop
Frontier Logo
1:27 pm - 8:07 pm
SJO
-
MDW
29h 40m
1 stop
$445Frontier
Sat, Apr 4 - Thu, Apr 9
Multiple Airlines Logo
6:30 am - 3:05 pm
MDW
-
SJO
9h 35m
1 stop
Multiple Airlines Logo
7:45 am - 10:19 pm
SJO
-
MDW
13h 34m
2 stops
$452Multiple Airlines
Mon, Apr 13 - Thu, Apr 16
Frontier Logo
6:00 am - 12:12 pm
MDW
-
SJO
7h 12m
1 stop
Frontier Logo
10:06 am - 11:05 pm
SJO
-
MDW
11h 59m
1 stop
$453Frontier
Thu, Apr 2 - Sat, Apr 11
Multiple Airlines Logo
7:30 am - 10:38 am
MDW
-
SJO
28h 08m
2 stops
Multiple Airlines Logo
4:35 pm - 1:00 pm
SJO
-
MDW
19h 25m
2 stops
$458Multiple Airlines
Tue, Apr 14 - Fri, Apr 17
Southwest Logo
5:35 am - 12:10 pm
MDW
-
SJO
7h 35m
1 stop
Southwest Logo
1:10 pm - 11:05 pm
SJO
-
MDW
8h 55m
1 stop
$474Southwest
Mon, Apr 20 - Wed, Apr 29
Southwest Logo
7:30 am - 7:00 pm
MDW
-
SJO
12h 30m
2 stops
Southwest Logo
9:00 am - 7:45 pm
SJO
-
MDW
9h 45m
2 stops
$478Southwest
Mon, Apr 27 - Tue, May 5
Southwest Logo
12:10 pm - 7:00 pm
MDW
-
SJO
7h 50m
1 stop
Southwest Logo
1:10 pm - 9:55 pm
SJO
-
MDW
7h 45m
1 stop
$479Southwest
Thu, Apr 9 - Thu, Apr 16
Frontier Logo
2:56 pm - 12:12 pm
MDW
-
SJO
22h 16m
1 stop
Frontier Logo
1:27 pm - 8:07 pm
SJO
-
MDW
29h 40m
1 stop
$480Frontier
Sat, Apr 4 - Thu, Apr 9

Frontier flights from Chicago Midway Airport to San José

Our best Frontier deals on Chicago Midway Airport to San José flight tickets
Frontier
Apr 8
MDW2:56 pmChicago Midway
22h 16m
1 stop
SJO12:12 pmSan José Juan Santamaria Intl
May 29
SJO9:35 amSan José Juan Santamaria Intl
35h 27m
2 stops
MDW10:02 pmChicago Midway
$395
Frontier
Apr 2
MDW6:00 amChicago Midway
7h 12m
1 stop
SJO12:12 pmSan José Juan Santamaria Intl
Apr 11
SJO10:06 amSan José Juan Santamaria Intl
11h 59m
1 stop
MDW11:05 pmChicago Midway
$413
Frontier
Apr 4
MDW2:56 pmChicago Midway
22h 16m
1 stop
SJO12:12 pmSan José Juan Santamaria Intl
Apr 11
SJO10:06 amSan José Juan Santamaria Intl
11h 59m
1 stop
MDW11:05 pmChicago Midway
$426

Southwest flights from Chicago Midway Airport to San José

Our best Southwest deals on Chicago Midway Airport to San José flight tickets
Southwest
Apr 20
MDW5:35 amChicago Midway
7h 35m
1 stop
SJO12:10 pmSan José Juan Santamaria Intl
Apr 29
SJO1:10 pmSan José Juan Santamaria Intl
8h 55m
1 stop
MDW11:05 pmChicago Midway
$474
Southwest
Apr 27
MDW7:30 amChicago Midway
12h 30m
2 stops
SJO7:00 pmSan José Juan Santamaria Intl
May 5
SJO9:00 amSan José Juan Santamaria Intl
9h 45m
2 stops
MDW7:45 pmChicago Midway
$478
Southwest
Apr 9
MDW12:10 pmChicago Midway
7h 50m
1 stop
SJO7:00 pmSan José Juan Santamaria Intl
Apr 16
SJO1:10 pmSan José Juan Santamaria Intl
7h 45m
1 stop
MDW9:55 pmChicago Midway
$479

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to San José that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated March 22, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San José that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 4/8

2:56 pm-12:12 pm

1 stop22h 16m

San José Juan Santamaria Intl

Fri 5/29

9:35 am-10:02 pm

2 stops35h 27m

$395

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 4/4

2:56 pm-12:12 pm

1 stop22h 16m

San José Juan Santamaria Intl

Sat 4/11

10:06 am-11:05 pm

1 stop11h 59m

$426

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 4/4

2:56 pm-12:12 pm

1 stop22h 16m

San José Juan Santamaria Intl

Thu 4/9

1:27 pm-8:07 pm

1 stop29h 40m

$445

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 4/13

6:30 am-3:05 pm

1 stop9h 35m

San José Juan Santamaria Intl

Thu 4/16

7:45 am-10:19 pm

2 stops13h 34m

$452

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 4/2

6:00 am-12:12 pm

1 stop7h 12m

San José Juan Santamaria Intl

Sat 4/11

10:06 am-11:05 pm

1 stop11h 59m

$453

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 4/14

7:30 am-10:38 am

2 stops28h 08m

San José Juan Santamaria Intl

Fri 4/17

4:35 pm-1:00 pm

2 stops19h 25m

$458

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 4/20

5:35 am-12:10 pm

1 stop7h 35m

San José Juan Santamaria Intl

Wed 4/29

1:10 pm-11:05 pm

1 stop8h 55m

$474

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 4/27

7:30 am-7:00 pm

2 stops12h 30m

San José Juan Santamaria Intl

Tue 5/5

9:00 am-7:45 pm

2 stops9h 45m

$478
Quickest round-trip

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 4/9

12:10 pm-7:00 pm

1 stop7h 50m

San José Juan Santamaria Intl

Thu 4/16

1:10 pm-9:55 pm

1 stop7h 45m

$479

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 4/4

2:56 pm-12:12 pm

1 stop22h 16m

San José Juan Santamaria Intl

Thu 4/9

1:27 pm-8:07 pm

1 stop29h 40m

$480

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to San José from

How to get the cheapest flight ticket from Chicago Midway Airport to San José

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to San José?

On average, the least expensive day to fly to San José from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $508. However, this price may fluctuate depending on the airline, the season, and holidays. Flights from Chicago Midway Airport to San José on a Saturday will generally be more expensive and average around $686. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to San José?

Our data shows that the cheapest Chicago Midway Airport to San José flights are usually those with departure times in the afternoon. Our users have found flights to San José in the afternoon for as low as $506. Flights at noon are often more expensive with an average ticket price of $664.

When to book flights from Chicago Midway Airport to San José

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to San José according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to San José (MDW to SJO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San José

Fastest flight time

6h 55m

Direct flights

None
The fastest flight from Chicago Midway Airport to San José takes 6h 55m
There are no direct flights from Chicago Midway Airport to San José. There are no popular flight routes from Chicago Midway Airport to San José.
Search flight deals

  • How far is Chicago Midway to San José Juan Santamaria Intl by plane?

    A flight from Chicago Midway to San José Juan Santamaria Intl will travel around 2210.5 mi. Typically, this will take 6h 55m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    Prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

  • How old do you have to be to fly from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to San José Juan Santamaria Intl Airport.

  • What documentation or ID do you need to fly to San José Juan Santamaria Intl Airport?

    The travel and health documents you'll need for your trip to San José Juan Santamaria Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San José Juan Santamaria Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago Midway Airport to San José?

Best airlines flying from Chicago Midway Airport to San José

Compare and see reviews for airlines that fly from Chicago Midway Airport to San José with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $394Free CancellationRating
8.0
4,324 reviews
Search Southwest flights

Traveling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Manuel Antonio
Jacó
Monteverde
Alajuela
Heredia
Dominical
San Gerardo de Dota
Santa Elena
Esterillos Este

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San José?

Finding the right flight to San José from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to San José quick and easy, saving you time and money.

Can I find flights from Chicago to San José with flexible booking policies on momondo?

All flight searches from Chicago to San José on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to San José?

momondo provides multiple filters to help you find the best flight to San José from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to San José right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to San José flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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